Dipeptidyl peptidase-IV inhibitory activity of dimeric dihydrochalcone glycosides from flowers of Helichrysum arenarium

Abstract

A methanol extract of everlasting flowers of Helichrysum arenarium L. Moench (Asteraceae) was found to inhibit the increase in blood glucose elevation in sucrose-loaded mice at 500 mg/kg p.o. The methanol extract also inhibited the enzymatic activity against dipeptidyl peptidase-IV (DPP-IV, IC50 = 41.2 μg/ml), but did not show intestinal α-glucosidase inhibitory activities. From the extract, three new dimeric dihydrochalcone glycosides, arenariumosides V–VII (2–4), were isolated, and the stereostructures were elucidated based on their spectroscopic properties and chemical evidence. Of the constituents, several flavonoid constituents, including 2–4, were isolated, and these isolated constituents were investigated for their DPP-IV inhibitory effects. Among them, chalconaringenin 2′-O-β-D-glucopyranoside (16, IC50 = 23.1 μM) and aureusidin 6-O-β-D-glucopyranoside (35, 24.3 μM) showed relatively strong inhibitory activities.

Composition, Antioxidant Potential, and Antimicrobial Activity of Helichrysum plicatum DC. Various Extracts

“…An interesting feature of nonpolar DCM and ACN extracts is the presence of (poly)methoxylated flavones, i.e. dimethoxy- (49,53) and pentamethoxyflavones in DCME (46,47) and methoxy-(51, 52), dimethoxy- (50), and triethoxydimethoxy flavones in ACNE (54,55,57). [22] + + + arenol [23] + + + plicatipyrone analog [22] + arzanol [27] + + + heliarzanol [23] + + cycloarzanol [23] + helipyrone diacetate [25] + + methylarzanol [23] + + 3-[1-[3-acetyl-2,4,6-trihydroxy-5-(3-methyl-2-buten-1-yl)phenyl]ethyl]-6-ethyl-4-hydroxy-5-methyl-2H-pyran-2-one [23] + + auricepyrone [22], 23-methyl-6-O-desmethylauricepyrone [22] + helicerastripyrone [28] [29] + plicatipyrone analog [26]…”

“…Compound Class/Name EE DCME ACNE helichrysoside [51] + quercetin [40] + + tiliroside [52] + tiliroside analog [52] + kaempferol [41] + chalcone arenariumoside V [53], arenariumoside VI [53], arenariumoside VII [53] + tomoroside A [53] + isosalipurposide [40] + helilupolone [54] + Terpenoid sesquiterpenoid sesquiterpene derivative [55][56][57] + sesquiterpene derivative [55][56][57] + sesquiterpene derivative [58][59][60] + sesquiterpene derivative [61,62] + sesquiterpene derivative [62][63][64] + eudesmane derivative [65] + sesquiterpene derivative [66][67][68] + sesquiterpene derivative [66][67][68] + ainsliaside E [69] + cinnamoyloxy-hydroxyeudesmane [70] + athrolide C [71] + + athrolide D [71] + diterpenoid diterpene derivative [30,72] + 8-(acetyloxy)-3-ethenyloctahydro-10-hydroxy-3,4a,7,7,10a-pentamethyl-1H-naphtho[2,1-b]pyran-2,5(3H,4aH)-dione [72] + (7-ethenyl-1,2,3,4,4a,4b,5,6,7,8,10,10a-dodecahydro-1,4a,7-trimethyl-1-phenanthrenyl)methyl-butanedioic acid methyl ester [72] + ent-kaurane derivative [73] + gymnospermin …”

A Review of Biologically Active Natural Products from a Desert Plant <i>Cistanche tubulosa</i>

“…Therefore improving postprandial hyperglycemia may form part of the strategy for the prevention and management of cardiovascular disease in diabetes. 136) We previously reported that several antidiabetogenic therapeutic candidates were obtained from natural resources such as Kochia scoparia, 137) Borassus flabellifer, 138) Solanum lycocarpum, 139) Sinocrassula indica, 140) Shorea roxburghii, 141) Helichrysum arenarium, 142) and Salacia reticulata, S. oblonga, and S. chinensis [143][144][145][146][147][148] evaluated by postprandial hyperglycemia in sugar-loaded rats and/or mice models. In these experiments the effects of the principal phenylethanoid glycosides from the stems of C. tubulosa, echinacoside (28) and acteoside (29), on postprandial increase in blood glucose levels in starch-loaded mice were examined.…”

“…These findings suggest that an aldose reductase inhibitor may have the capacity of preventing and/or treating several diabetic complications. 153) As potent aldose reductase inhibitors from natural resources, we identified several flavonoids, [154][155][156][157][158][159][160] stilbenoids, 141,154) terpenoids, 161) and quinic acid derivatives. 159) As shown in Table 8, several phenylethanoid glycosides, echinacoside (28, IC 50 = 3.1 µM), acteoside (29, 1.2 µM), kankanoside J 1 (35, 9.3…”

Effects of herbal multicomponent dietary supplement in experimental pneumonia

“…An increase of mitochondrial enzyme activity occurred with extracts of Potentilla anserine L [11]. Three other plants used in VL improve incretin secretion and, hence, insulin synthesis, and show a hypoglycemic activity; Helichrysum arenarium L. Moench [16], Anethum graveolens L [6] and Melissa officinalis [17].…”